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Old 08-29-2010, 08:36 AM   #61
Lorna
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well some of these weren't embarrassing dares, just embarrassing moments out of my life...

anyway, when I was about 17 I was dared to walk around the neighborhood in broad daylight in a short black skirt, black pumps and a top that revealed a lot of cleavage and walk in a really promiscuous fashion with my ass moving all about. Well, when I was doing it, this car slowed down behind me. I kept up the slutty walk, with my thighs rubbing together and my ass cheeks swaying from side to side. When the car passed me, I looked inside and there was a mother and her 11 or 12 year old son in the car, looking back at me and laughing HYSTERICALLY. I felt so humiliated I can't even imagine what a little whore I looked like with my ass swinging from side to side in that short, short skirt while I was walking down the streets. Only the people who were behind me know!

Another time, I was dared to stand in front of an open window in just t-shirt and a pair of underpants. It was broad daylight and I stood there for a while in front of a full length window with the shade pulled up all the way. Well, a work van passed by with two guys looking out the window, and a small vehicle with an old guy in it passed by and the guy was looking at me laughing! Also, some lady passed by and got a good look at me in my panties.

This other one wasn't a dare, but, back in high school, I'd worn a low cut top to school one day. I heard one of the girls in my class whispering to her friend that she didn't think it was fair that I got away with wearing that slutty of a top to school. So she went and reported it to the principal. I got called to the principal's office and a call was made to my parents to bring me a different t-shirt to wear. Only, neither of them could bring me a change of clothes. So, one of the ladies at the front office smirked at me and said, "Why don't you just wear your shirt backwards?" I was really embarrassed because the shirt I was wearing was in such a style that it was OBVIOUS when it was worn backwards, but I had no choice but to go into the bathroom in the nurse's office and flip my shirt around and wear it BACKWARDS the rest of the day, with the neckline chafing against my neck and the tag half-sticking out. I saw the girl who'd reported on me for wearing a low cut shirt and she grinned mockingly and said, "Next time don't dress like a slut." I felt so humiliated, but also excited by the embarrassment, so I decided to embarrass myself even more by pulling the tag on the neckline out ALL the way and wearing it like that the rest of the day. It was quite humiliating to get little smirks from the other girls. Finally, I couldn't handle it and I rushed to the bathroom at the end of the day and masturbated with my bare butt on the toilet seat really hard.
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Old 09-28-2010, 04:09 AM   #62
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One of my most embarrassing dares was being driven round town naked with my wife sat next to me in the backseat pleasuring me while my mate drove with his mrs sat next to him .I was the only one naked and they made sure I was seen many times .They thought it was hilarious.Wouldnt have been so funny if someone had reported us.Got to admit though it was a rush.
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Old 10-04-2010, 09:44 AM   #63
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Take photographs of myself naked (face blocked out) and leave them in semi-public places (public toilets, etc).

Embarassing because I'm overweight, not sure why I felt that way since no one knew it was me :P
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Old 10-11-2010, 06:34 AM   #64
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I was once made to masterbate in the office while others were near by. I did not get caught but I really felt embarrassed to do it.
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Old 04-07-2011, 12:38 PM   #65
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My friends dad is a cop so while he was at work there were extra handcuffs in the house so they tied my hands in one handcuff my feet in another then cuffed me to the pole outside and my friends took my clothes and said i could have them back in 1 minute but instead they hid them and took pictures as black mail and didnt give me my clothes back until 6am and they had to be able to keep the pics as black mail.. worst dare ever
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Old 04-07-2011, 09:48 PM   #66
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i had to go to a little bistro around the corner wearing only high heels and a towel, but if towel dropped i couldnt pick it up and contineu the dare nude.
i was lucky it didnt drop lol
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Old 10-24-2011, 11:08 PM   #67
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A really embarrasing dare, me and my sister got really drunk with some friends, she dared me to get naked with her and stick my ahem, in her pussy cat, the next day I got emailed the photos, and I think she got them to because she seemed to act really strangely around me for a few days.
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Old 10-25-2011, 06:39 AM   #68
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My then girlfriend masturbated me to full erection, put a cock ring on to keep it like that, and sent me to the supermarket with just trackie trousers on my lower half. I stuck out a mile. Everyone just stared at me, very humiliating, but a huge turn on as well
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Old 10-25-2011, 05:23 PM   #69
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to get fully X-dressed in public infront of my girlfreind, and then to piss myself and give myself a hanging wedgie from a nearby tree with cooked pasta in the back and front of the panties i was wareing.
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Old 12-25-2011, 09:09 PM   #70
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the MOST embarassing dare was this:
one time me and my friends were at a pool party and started playing truth or dare,.i somehow just got stuck with THE MOST EMBARASSING dare on the list,..i had to get into my bikini while all my friends r fully clothed and sitting on the beach chairs by the pool, i had to wet myself in the pool and get out then kneel with my shoulder on the ground (butt sticking up) next to this guy that everyone picked, he had to spank me on my butt for 20times or sth, and i had to moan each time he spanks me and say thank you,...i died of embarassment,.but i was rly turned on,...>////<
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Old 12-28-2011, 01:35 AM   #71
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I was about 12 and had to lay on top of the jungle jim naked for 10 minutes.
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Old 12-28-2011, 03:28 PM   #72
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The most embarrassing dare, at the time, was in 5th grade I was dared to wear a thong, wedgie it, and bend over and show it to the guy I liked at school. It was really embarrassing then and I'm not sure if I would do that even now. I didn't even own a thong then, I had to borrow one from my friend. :/
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Old 12-30-2011, 03:25 AM   #73
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i guess, now that i think about it, i had to get fully naked at a party and pose for photos for a full hour
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Old 12-30-2011, 06:17 AM   #74
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the most embarrassing dare i had to do was suck my little bros dick(not very pleasant and so embarrassing).
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Old 12-30-2011, 02:37 PM   #75
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Once I was playing Tord at a friends place and was dared to moon the first person enters in the room and guess what it was my friends mom and she was stunned after that and I can not face her for a long long period. it was really very humiliating and embarrassing
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